Method for producing 1,3-dimethyladamantane

a technology of dimethyladamantane and 1,3-dimethyladamantane, which is applied in the direction of organic chemistry, chemical apparatus and processes, hydrocarbon preparation catalysts, etc., can solve the problems of low yield of 38.7%, high cost of pt and re in the catalyst, and no selective production method of 1,3-dimethyladamantane at a high yield by using hf.bf/sub>catalys

Active Publication Date: 2015-07-21
MITSUBISHI GAS CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0024]According to a method of the present invention, no solvent is used. Therefore, a step of removing a solvent and a denatured substance thereof is not necessary. In addition, no costly catalyst is required, and a catalyst used can be recovered. Thus, 1,3-dimethyladamantane can be produced at a high yield and advantageously in terms of cost while environmental load is reduced.

Problems solved by technology

However, the method of obtaining 1,3-dimethyladamantane from PHA has problems that the yield is as low as 38.7% and that Pt and Re in the catalyst are costly.
However, no method of selectively producing 1,3-dimethyladamantane at a high yield by use of HF.BF3 catalysts is known so far.
However, in order to obtain 1,3-dimethyladamantane at a high yield, it is indispensable to use 1,2-dichloroethane, which is costly, as a catalyst component.
In addition, aluminum chloride is not reusable and thus a large amount of waste derived from aluminum chloride is generated.
For these reasons, the method of using aluminum chloride is not industrially advantageous (Patent Document 5).

Method used

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  • Method for producing 1,3-dimethyladamantane
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  • Method for producing 1,3-dimethyladamantane

Examples

Experimental program
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example 1

[0044]PHA was subjected to an isomerization reaction by use of a Hastelloy autoclave having a capacity of 0.5 L and including an electromagnetic stirring device, a heating device, a gas and liquid supply opening and a reaction product discharge opening. 50 g (2.5 mol) of HF produced by Morita Chemical Industries Co., Ltd. and 100 g (0.6 mol) of PHA were put to a reactor, and 16 g (0.24 mol) of BF3 produced by Stella Chemifa Corporation was supplied. Then, these substances were heated to a temperature of 100° C. by the heating device with no solvent, and stirred for 4 hours while the temperature was kept at 100° C. The reaction product solution was sampled. The yield of 1,3-dimethyladamantane was 77% with respect to PHA as the material. The yield of 1-ethyladamantane as an intermediate was 15% with respect to PHA as the material, while no high boiling point compound was observed. Then, as a result of being left still, the reaction product solution was divided into two layers, namely,...

example 2

[0045]A reaction was carried out under substantially the same conditions as those in Example 1 except that HF and BF3 recovered in Example 1 were used. The yield of 1,3-dimethyladamantane was 75%, and deactivation of the catalysts was not observed. Like in Example 1, no high boiling point compound was observed.

example 3

[0046]PHA was subjected to an isomerization reaction by use of a Hastelloy autoclave having a capacity of 0.5 L and including an electromagnetic stirring device, a heating device, a gas and liquid supply opening and a reaction product discharge opening. 50 g (2.5 mol) of HF produced by Morita Chemical Industries Co., Ltd. and 100 g (0.6 mol) of PHA were put to a reactor, and 16 g (0.24 mol) of BF3 produced by Stella Chemifa Corpration was supplied. Then, these substances were heated to a temperature of 80° C. by the heating device with no solvent, and stirred for 4 hours while the temperature was kept at 80° C. The reaction product solution was sampled. The yield of 1,3-dimethyladamantane was 51% with respect to PHA as the material. The yield of 1-ethyladamantane as an intermediate was 42% with respect to PHA as the material, while no high boiling point compound was observed. Then, as a result of being left still, the reaction product solution was divided into two layers, namely, an...

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Abstract

According to the present invention, a method can be provided for producing 1,3-dimethyladamantane represented by formula (2) by performing a skeletal isomerization reaction using, as catalysts, 0.5 to 1 .5 parts by weight of HF and 0.05 to 0.5 parts by weight of BF3 with respect to 1 part by weight of perhydroacenaphthene represented by formula (1) under a reaction temperature of 60 to 110° C.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This Application is a U.S. National Stage Application filed under 35 U.S.C. §371 of International Application PCT / JP2011 / 075694, filed Nov. 8, 2011, designating the United States, which claims priority from Japanese Patent Application 2010-254189, filed Nov. 12, 2010, the complete disclosures of which are hereby incorporated herein by reference in their entirety for all purposes.TECHNICAL FIELD[0002]The present invention relates to a method for producing 1,3-dimethyladamantane represented by the following formula (2) industrially advantageously from perhydroacenaphthene represented by the following formula (1) by use of HF.BF3 catalysts.[0003]BACKGROUND ART[0004]1,3-dimethyladamantane is expected to be useful as a material of various types of fine chemicals including pharmaceutical drugs, and a dicarboxylic acid and a diol thereof are expected to be useful as a highly functional polymer material.[0005]Conventionally, Patent Document 1 des...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C13/28C07C5/31C07C5/29
CPCC07C5/31C07C5/29C07C13/615C07C2103/20C07C2103/74C07C2527/1206C07C2527/1213C07C2603/20C07C2603/74C07C5/22C07B61/00
Inventor MATSUURA, YUTAKAKITAMURA, MITSUHARU
Owner MITSUBISHI GAS CHEM CO INC
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